SimonTheSalesBooster Skill: Social Selling Daily Routine
What This Skill Does
Generates a structured, time-boxed daily LinkedIn social selling routine that moves prospects through awareness → connection → conversation → meeting. Produces a repeatable 45-minute daily action plan with specific tasks, message templates, and tracking metrics.
When to Use
- You want to build pipeline through LinkedIn without cold calling
- Your team needs a consistent daily social selling habit
- You want to turn LinkedIn activity into booked meetings
- You're building a personal brand that attracts inbound leads
Inputs Required
Before running this skill, ask the user for:
- Time available per day — 20 min, 45 min, or 90 min?
- Primary goal — more connections, more conversations, or more booked meetings?
- Target prospect profile — who are they trying to reach?
- Current LinkedIn activity level — posting frequency, connection count, SSI score if known
- CRM or tracking tool — how do they currently track LinkedIn activity?
Step-by-Step Instructions
Step 1 — Design the Daily Routine Block
Build a time-blocked daily schedule based on available time:
45-Minute Daily Routine (Recommended)
[0:00–0:05] Morning Scan — Check notifications, accept relevant connection requests, note who engaged with your content
[0:05–0:15] Engage First — Comment on 5 posts from target prospects (add value, don't pitch)
[0:15–0:25] Warm Outreach — Send 5 personalized connection requests to Tier 1 prospects
[0:25–0:35] Move Conversations Forward — Follow up with 3–5 accepted connections (move toward meeting)
[0:35–0:45] Content Window — Write or schedule 1 post (or engage with 5 more posts if no content today)
Step 2 — Connection Request Templates
Create 3 non-pitch connection request templates (300 character limit):
Template A — Trigger Event:
Hi [Name], saw [Company] just [raised funding / hired a new VP / hit a milestone] — congrats! I work with [similar companies] on [relevant topic]. Would love to connect.
Template B — Content Engagement:
Hi [Name], your post about [topic] resonated with me — especially the part about [specific detail]. I work in a similar space and would love to be in your network.
Template C — Mutual Signal:
Hi [Name], noticed we both know [Mutual Connection] and work in [shared space]. Always great to connect with people navigating [industry challenge].
Step 3 — Conversation Progression Sequence
Once connected, use this sequence to move to a meeting (never pitch on message 1):
Day 1 — The Value Drop:
Hey [Name], glad to be connected! I recently [wrote a piece / put together a resource] on [relevant topic] — thought it might be useful given what you're working on at [Company]. Happy to share if it's helpful.
Day 4–5 — The Soft Offer:
Hey [Name], curious — how are you currently handling [pain point]? I've been talking to a lot of [title] at companies like yours and [insight/pattern you've noticed]. Would love to get your perspective.
Day 8–10 — The Ask:
[Name], based on our conversation / what you shared — I think there could be a real fit here. Would a quick 20-min call make sense to explore? No pressure either way.
Step 4 — Content Strategy for Social Selling
Great content pulls prospects to you. Recommend a weekly content mix:
| Day | Content Type | Goal |
|---|---|---|
| Monday | Insight post (data point or observation from your market) | Establish authority |
| Wednesday | Story post (customer success or lesson learned) | Build trust |
| Friday | Question/poll post (invite engagement from prospects) | Generate conversations |
Content Formula that Works:
Line 1: Bold hook (problem or counterintuitive statement)
Line 2: Blank line (forces "see more" click)
Lines 3–7: The insight or story (3–5 punchy bullets or short paragraphs)
Line 8: Blank
Line 9: CTA — question to drive comments or soft offer
Step 5 — Tracking Dashboard
Create a simple weekly tracking table:
| Metric | Daily Goal | Mon | Tue | Wed | Thu | Fri | Weekly Total |
|--------|-----------|-----|-----|-----|-----|-----|-------------|
| Connection requests sent | 5 | | | | | | |
| Acceptance rate | >40% | | | | | | |
| Follow-up messages sent | 5 | | | | | | |
| Reply rate | >20% | | | | | | |
| Meetings booked | 1–2/week | | | | | | |
| Posts published | 3/week | | | | | | |
| Comments left | 5/day | | | | | | |
Output Format
Deliver:
- Time-blocked daily routine (customized to available time)
- 3 connection request templates (ready to use)
- 3-message conversation progression sequence
- Weekly content calendar with post formulas
- Weekly tracking dashboard
Pro Tips
- Comments are the most underrated social selling move — a thoughtful comment on a prospect's post gets you noticed without being salesy
- Never send a pitch in the first 3 messages — LinkedIn users are conditioned to disconnect the second they feel sold to
- The best time to post on LinkedIn: Tuesday–Thursday, 7–9am or 12–1pm (user's local time)
- Use LinkedIn's "Who Viewed Your Profile" daily — these are warm signals, reach out within 24 hours
- If your connection request acceptance rate is below 30%, your message or targeting is off — A/B test immediately